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Craig Elson’s life has hit rock bottom. Even though he’s one of the best strategic planners around, a more confident guy takes credit for his work, and despite being a good-looking man, he suffers insults from the slimiest creep at the bar. Taking care of his beloved mom, who has Alzheimer’s, uses all his funds, leaving him in a plain, depressing car… and a plain, depressing life.

Until he sees gorgeous grad student Jesse Randall and his T-shirt that reads “I Would Bottom You So Hard.” The message seeps into Craig’s soul, and he asks Jesse to teach him to top.

Jesse’s had his eye on the quiet hottie who comes into the coffee shop, and he’s more than eager to perfect his tutoring. He sets out to get Craig a new job, a new apartment, and a new life so far outside plain and depressing that it’s unrecognizable.The problem is, Craig loves his lessons—and his teacher—too much to want to graduate. How can Craig reach the top without losing his sassy bottom?